This BOS is curated by Juliana Engberg under the title You Imagine What You Desire. A major part of any large exhibition is about trying to make sense of the curatorial gambit, but this isn’t so much a themed show as a loosely connected grouping of works based on the idea the audience communes with the artist via the artwork. It’s all about entering your imagination zone and letting the artist suggest ideas, themes and concepts that are, in the curator’s view, a kind of “active philosophy”.

It sounds slightly over the top, but Engberg believes artists are the vanguard of society, calling them the “forward thinkers” who dream up improbable but insightful ways of reimagining the world. The curator’s preference, therefore, is for art that is playful and engaging, not too demanding on a conceptual level, but which has its own integrity, and a poetic outlook.

Belgium artist Tinka Pittoors in front of her artwork Dysideological Principle at Carriageworks, Sydney. Photograph: Anna Kucera for the Guardian

Cockatoo Island has become the public focal point of the BOS since it was first used as a venue back in 2008. It’s where the big, eye-catching works are sited, those mammoth pieces that become the icons of the whole show and that have enough wow factor to entertain families on a day trip.

Cockatoo’s Turbine Hall offers up two major pieces – Stone and Singer (2014) a performance by Tori Wranes, and a video projection I am the River (2012) by Eva Koch. While they might not have the same visual impact as works in previous Biennales, Wranes’s weird musical performance, which sees the artist made up as a kind of mutant singing a strange song beneath a giant swinging stone, and Koch’s never-ending waterfall, are possibly the most enjoyably accessible works on the island. An installation by Mikala Dwyer, The Hollows (2014) is a gorgeous if physically remote sculptural work, while Ulla Von Brandenburg’s Street, Play, Way (2014), is an installation video piece that successfully incorporates the decrepit ambience of Cockatoo’s industrial past into a dreamlike experience.

Stone from performance by Tori Wranes; Background, I am the River by Danish artist Eva Koch. Photograph: Anna Kucera for the Guardian

Unfortunately few of Cockatoo’s other works match these highlights. Many are very slight video pieces, such as Marko Lulic’s Space-Girl Dance (2009), which features a costumed performer disco dancing in a park. It’s not as though Australia doesn’t already produce enough of that kind of work itself to be importing such pointless frivolity from Austria. Callum Morton’s The Other Side (2014) promises much for the visitor. A miniature train plunges passengers through a Google search engine – a poster mounted on a billboard – into the Long Tunnel, the island’s stone passageway dressed up with lights, spooky sounds and dry ice. When you get to the other end of it all you can think is: is that it?

The Other Side by Australian artist Callum Morton. Photograph: Anna Kucera for the Guardian

The Museum of Contemporary Art is what Enberg says is a “surrealistic experience”, and the emphasis here is on big space: not so much on the depiction of space in art, but rather space around the art – and lots of it. There are two floors of Biannale art at the MCA, and one is given over to just two works – an installation by Jim Lambie, and a gigantic video installation by Pippilotti Rist. Lambie’s work is attractive but largely superficial – a room with coloured stripes on its floor – but it is Rist’s Mercy Garden Retour (2014) that demands your attention – a cosmic encounter with images of the ocean, of washing on a line and a fleeting image of the largest uncircumcised penis you are ever likely to see in an artwork.

Jim Lambie with his work Screamadelica at the Museum of Contemporary Art, Sydney. Photograph: Anna Kucera for the Guardian

Rist’s video is about tactility and touch, and viewers are offered cushions on the floor in the shape of human torsos to lounge around on as they take in the spectacle. The work is genuinely mad in a way that many artworks that aspire to the surreal simply cannot achieve. An installation upstairs at the MCA by Douglas Gordon, Phantom (2011), is attractive but it’s let down by a nostalgia for surrealist imagery that is profoundly cliched regardless of its high-gloss presentation. Elsewhere at the MCA there are collages, faux-modernist sculpture, photographs of abstract statuary, and a spooky video by Ann Lislegaard of two talking owls.

The Art Gallery of NSW offers more of that familiar surrealist mojo but there are a few surprises in store. A video by Angelica Mesiti, In the Ear of the Tyrant (2013-14) doesn’t expect its audience to sit through an hour or more of faux-cinematic art to get to its idea: a woman wanders through what appears to be a location somewhere in the Middle East, her voice singing out a plaintive song into the echoing space of an empty building. Its precision, brief running time and gorgeous cinematography mark it out as one of the most successful pieces in the entire Biennale. A similarly intriguing work by Rosa Barba, Time as Perspective (2012), is a film about film itself, and of the landscape as an experience of time. Shown as a 35mm film loop, the work sits in a gallery space through which people are obliged to walk, and they cut through the image confusing a linear reading of the movie. It’s unclear whether that installation was intended but it still works brilliantly.

Volunteers participate in a performance-work by artist Egl Budvytyt outside the Art Gallery of New South Wales, Sydney. Photograph: Anna Kucera /The Guardian

The rise of video art over the past 15 years has had a profound effect on the way people experience contemporary art. Where once we may have encountered an occasional film projection or a TV set in a room, the moving image has become one of the generic features of the gallery experience. Yet no one has quite worked out how to exhibit a video or film work in a gallery successfully because the way in which we watch a narrative on screen is so different to the way we look at art in a gallery. It just feels wrong somehow to try to take in a longform work in a gallery and I often think of something that artist Tony Schwensen once said to me – if a video or film is going to run for 90 minutes then there should be comfy chairs, popcorn and choc-tops.

In what must be the most ambitious part of this BOS, Carriageworks has been given over to a series of installations that attempts to tackle that curatorial conundrum. A vast space has been created inside the venue’s already cavernous halls to accommodate videos and film works that run the gamut from the familiar to the grandiose. A video work such as Daniel McKewen’s Running Men (2008-14), five screens of men from Hollywood movies running, is the kind of piece often seen in Australian galleries, but Mathias Poledna’s A Village by the Sea (2011) is testament to the scale of production available to international artists.

Poledna’s work quotes 1930s Hollywood musicals and features the artist performing a sappy romantic song dressed in tux and silk scarf in a faithfully reproduced period set. The work’s art direction, camera work and staging are a painfully accurate rendition of a half-remembered genre, sitting somewhere between pastiche and waking nightmare. Throughout Carriageworks more and more film and video pieces offer the viewer glimpses of ambitious and large-scale moving image works, all too detailed and demanding to take in. As if to cover their bases, the BOS also offers a 16-hour program of films shown in a traditional cinema setting.

There is one more BoS venue at Artspace but You Imagine What You Desire ultimately defeated me. I needed to go outside and get away from the art.

As a single viewing experience the BOS lacks cohesion and many of its works come off as slight and inconsequential. The overall problem is a lack of a strong curatorial connection between the works. It’s all very well to allow the viewer some agency in the experience of the art, but if the artists are going to communicate ideas and to be allowed to be the avant-garde thinkers Engberg claims, then the curatorial process needs to bring out the connections beyond a vague grouping by type.

In Engberg’s hands we have a Biennale that, after all the politics and grandstanding, just doesn’t amount to much. We can spend a lot of time working out what it means, and how and why all of this might go together, but that isn’t the same as experiencing a work of art that tells you something, or makes you feel something, or leaves you with an impression of something beautiful in the world. That is something we can imagine, and it is something that we desire.

Emerging from the shadow of scandal which proceeded it like no other Biennale in recent times, the 2014 Biennale of Sydney is set to wow crowds from the Museum of Contemporary Art to the Art Gallery of NSW and across the water to Cockatoo Island, home of the bigger installations. It's all aboard the Google train for this year's festival of art